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As Puerto Rico prepares to hold its first status referendum in 14 years this November, a leading advocate for D.C. statehood said he sees strong parallels between the two jurisdictions’ political situations.

Democrat Paul Strauss, elected to his third term as a symbolic “shadow” U.S. senator for the District in 2008, said he is an “interested observer” watching the decades-old status debate in Puerto Rico. That debate may come to a head on Election Day, Nov. 6.

“The similarities aren’t lost on me, and the fact that states have frequently been admitted in pairs … is also not lost on me,” Mr. Strauss said. “I think this is a step along the journey for Puerto Rico as it is for the District of Columbia.”

Sen. Jamin B. Raskin, Montgomery Democrat, a constitutional law expert who has testified in favor of D.C. statehood, said he agrees.

“History tells us that most states admitted to the Union after the original 13 came in pairs … like animals on Noah’s Ark,” Mr. Raskin said. “So it’s possible that D.C. could try to link its cause to Puerto Rico in the event that the Puerto Rican statehood movement takes off.”

As the Constitution stipulates a federal district for the seat of the government, the admission of the entire District as a state would require a constitutional amendment, something Mr. Raskin said he does not believe would succeed.

“Statehood for the District would require shrinking the federal district down to the White House, the Capitol and the federal buildings, and ceding the [remaining] land to a new state,” Mr. Raskin said. “That would be the same process as retroceding the District to Maryland.”

Under the retrocession option, the city’s populated portions would return to Maryland, which ceded land north of the Potomac River to form the District in 1800. Precedent for this option dates back to the 1840s, when the District, which originally straddled both banks of the Potomac, lost modern-day Arlington County and Alexandria to Virginia.

James Joyner, the Alexandria, publisher of the political blog Outside the Beltway, prefers retrocession to statehood.

“Because of the strange constitutional structure we have, statehood means a representative, which probably wouldn’t be a problem, but it also means two senators,” Mr. Joyner said. “And it just doesn’t make sense to give a little rump of a city … equal representation to California.”

Mr. Joyner has also supported a modified form of retrocession wherein the District would remain intact as a congressional district and would retain significant control over its own affairs, though he acknowledges it would require a constitutional amendment.

But Maryland might benefit more from D.C. statehood than it would from retrocession, Mr. Strauss argued.

“I think if D.C. got statehood, it would be tremendous for Maryland. I think it would benefit Maryland greatly, probably Virginia as well,” Strauss said. “The interests of the D.C./Maryland region, or the Delmarva region, whatever you want to call it, are two votes short in the Senate.”

Mr. Strauss named Amtrak funding and Chesapeake Bay cleanup efforts as among the regional interests that could get a boost.

Mr. Raskin said that while he does not oppose retrocession, he does not believe there is much appetite for it either in the District or in Maryland.

“Politically, (retrocession) seems not to be on the table,” Mr. Raskin said. “At this point, it seems as if the energy is still focused on D.C. statehood.”

Maryland Gov. Martin O’Malley is not in favor of retrocession, according to his communications director, Raquel Guillory. However, she said, Mr. O’Malley does support D.C. statehood.

“Residents of [the District] have long deserved the right to have fair representation in their federal government,” Ms. Guillory wrote in an email characterizing Mr. O’Malley’s position. “For hundreds of years, D.C. has been our nation’s capital. D.C. should not lose its independence and identity simply to gain the same rights all the states enjoy.”

During the 1980s and early 1990s, D.C. statehood advocates wielding a ratified constitution for the “state of New Columbia” failed to win congressional approval. In 1993, the U.S. House of Representatives voted 277-193 against D.C. statehood.

Four of Maryland’s eight representatives voted against the 1993 bill. Of them, only Reps. Steny Hoyer, a Democrat, and Roscoe Bartlett, a Republican, remain in Congress.

Mr. Hoyer supported an unsuccessful 2009 effort to grant the District a voting representative in the House. His office did not respond to a request for comment.

Mr. Bartlett’s office would not elaborate on his current thinking.

“Until the legislation is going to advance through the committee process, it won’t come up for Congressman Bartlett,” said Lisa Wright, Mr. Bartlett’s press secretary.

Mr. Strauss said he blames the failure of D.C. statehood on several factors. One of them, he said, is congressional Republicans’ reticence to add new seats to the U.S. Senate that would favor Democrats. Another, he said bluntly, is “racism.”

According to Mr. Strauss, Congress “has had a history of racial profiling … when it comes to states that have entered the Union in the latter half of our nation’s history.” He said many of the objections raised to the statehood of Hawaii and New Mexico last century, including differences in language and racial composition, are now being raised to D.C. and Puerto Rican statehood.

Neil Weare, policy counsel at the Constitutional Accountability Center in the District, suggested that D.C. residents and residents of territories like Puerto Rico and Mr. Weare’s native Guam should work together in pushing for congressional representation and voting rights.

The District “and U.S. territories are really more alike than they are different, and working together would help make this a more bipartisan issue,” Mr. Weare wrote in an email.

But Mr. Strauss said that even if voters in Puerto Rico choose statehood in November, he is not confident that Congress, which constitutionally acts as the gatekeeper to the Union, will honor their decision.

“The regrettable fact is that while I think that the question of statehood should be up to the people of Puerto Rico, it’s not guaranteed,” Mr. Strauss said, invoking the House’s rejection of D.C. statehood in 1993.

There is some evidence, despite Mr. Strauss’s concerns, that the results of the Puerto Rico referendum could be recognized by the federal government. Republican presidential candidates Mitt Romney, Newt Gingrich and Rick Santorum backed the referendum last month while campaigning in Florida, with Mr. Romney saying he expects the outcome to be a vote for statehood.

President Obama has also pledged to honor the results of the referendum, though he cautioned last year that if no option wins decisively, Congress may not act on it.

Statehood will appear on Puerto Rico’s ballot alongside full independence and free association in the two-part question, which will also ask voters whether they want to change Puerto Rico’s political status at all.